EP0004408B1 - Verfahren zur Herstellung von 1,7-Octadien und zur Aktivierung eines für die Anwendung in diesem Verfahren geeigneten Katalysators - Google Patents

Verfahren zur Herstellung von 1,7-Octadien und zur Aktivierung eines für die Anwendung in diesem Verfahren geeigneten Katalysators Download PDF

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Publication number
EP0004408B1
EP0004408B1 EP79200140A EP79200140A EP0004408B1 EP 0004408 B1 EP0004408 B1 EP 0004408B1 EP 79200140 A EP79200140 A EP 79200140A EP 79200140 A EP79200140 A EP 79200140A EP 0004408 B1 EP0004408 B1 EP 0004408B1
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Prior art keywords
palladium
formic acid
phosphine
carbon atoms
butadiene
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Expired
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EP79200140A
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English (en)
French (fr)
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EP0004408A2 (de
EP0004408A3 (en
Inventor
Kenzie Nozaki
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Shell Internationale Research Maatschappij BV
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Shell Internationale Research Maatschappij BV
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0237—Amines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0239—Quaternary ammonium compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0255—Phosphorus containing compounds
    • B01J31/0267—Phosphines or phosphonium compounds, i.e. phosphorus bonded to at least one carbon atom, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, the other atoms bonded to phosphorus being either carbon or hydrogen
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/16—Reducing
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
    • C07C2/74—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition with simultaneous hydrogenation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/824—Palladium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/02—Sulfur, selenium or tellurium; Compounds thereof
    • C07C2527/053—Sulfates or other compounds comprising the anion (SnO3n+1)2-
    • C07C2527/054—Sulfuric acid or other acids with the formula H2Sn03n+1
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • C07C2527/24—Nitrogen compounds
    • C07C2527/25—Nitrates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C07C2531/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/22—Organic complexes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • C07C2531/24—Phosphines

Claims (12)

1. Verfahren zur Herstellung von 1,7-Octadien durch Hydrodimerisierung von Butadien in Gegenwart eines Komplexkatalysators aus einer Palladiumverbindung und einem Tris-(organo)-mono- phosphin, dadurch gekennzeichnet, dass der Katalysator mit einem Reduktionsmittel bei einer Temperatur von 20 bis 90°C kontaktiert wird, bevor er mit dem Butadien in Berührung gebracht wird.
2. Verfahren gemäss Anspruch 1, dadurch gekennzeichnet, dass die Kontaktzeit 0,1 bis 5 h beträgt.
3. Verfahren gemäss Anspruch 1 oder Anspruch 2, dadurch gekennzeichnet, dass die Palladiumverbindung Palladiumnitrat, Palladiumsulfat, Palladiumacetat oder Palladiumacetylacetonat ist.
4. Verfahren gemäss einem der vorstehenden Ansprüche 1 bis 3, dadurch gekennzeichnet, dass das Tris-(organo)-monophosphin die allgemeine Formel
Figure imgb0014
hat, wobei R1 ein Aralkyl- oder Cycloalkylrest oder ein verzweigter Alkyl- oder verzweigter Alkenylrest mit 3 bis 10 Kohlenstoffatomen ist, wobei die Verzweigung an einem Kohlenstoffatom stattfindet, das nicht mehr als 2 Kohlenstoffatome vom Phosphoratom entfernt ist, und R2 und R3 der Rest R1 sind oder unabhängig Alkylreste mit 1 bis 10 Kohlenstoffatomen, Alkenylreste mit bis zu 10 Kohlenstoffatomen oder Arylreste mit bis zu 10 Kohlenstoffatomen sind.
5. Verfahren gemäss Anspruch 4, dadurch gekennzeichnet, dass das Phosphin Tri(isopropyl)-phosphin ist.
6. Verfahren gemäss einem der vorstehenden Ansprüche, dadurch gekennzeichnet, dass das Reduktionsmittel Wasserstoff, Kohlenmonoxid, ein Trialkylamin- oder Ammoniumsalz der Ameisensäure, Hydrazin, Natriumborhydrid oder ein Trialkylphosphin ist.
7. Verfahren gemäss Anspruch 6, dadurch gekennzeichnet, dass das Reduktionsmittel das Triäthylaminsalz der Ameisensäure ist.
8. Verfahren gemäss einem der vorstehenden Ansprüche, dadurch gekennzeichnet, dass die Hydrodimerisierung des Butadiens in Gegenwart von Ameisensäure, einer Base, die die Ameisensäure neutralisieren kann, und gegebenenfalls eines Lösungsmittels durchgeführt wird.
9. Verfahren zur Aktivierung eines Komplexkatalysators aus einer Palladiumverbindung und einem Tris-(organo)-monophosphin, der für die Verwendung bei der Hydrodimerisierung von Butadien zur 1,7-Octadien geeignet ist, dadurch gekennzeichnet, dass der Katalysator mit einem Reduktionsmittel bei einer Temperatur von 20 bis 90°C kontaktiert wird.
10. Verfahren gemäss Anspruch 9, dadurch gekennzeichnet, dass die Kontaktzeit 0,1 bis 5 h beträgt.
11. Verfahren gemäss Anspruch 9 oder Anspruch 10, dadurch gekennzeichnet, dass das Reduktionsmittel Wasserstoff, Kohlenmonoxid, ein Trialkylamin- oder Ammoniumsalz der Ameisensäure, Hydrazin, Natriumborhydrid oder ein Trialkylphosphin ist.
12. Verfahren gemäss einem der Ansprüche 9 bis 11, dadurch gekennzeichnet, dass das Reduktionsmittel das Triäthylaminsalz der Ameisensäure ist.
EP79200140A 1978-03-27 1979-03-22 Verfahren zur Herstellung von 1,7-Octadien und zur Aktivierung eines für die Anwendung in diesem Verfahren geeigneten Katalysators Expired EP0004408B1 (de)

Applications Claiming Priority (2)

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US89011478A 1978-03-27 1978-03-27
US890114 1978-03-27

Publications (3)

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EP0004408A2 EP0004408A2 (de) 1979-10-03
EP0004408A3 EP0004408A3 (en) 1979-10-31
EP0004408B1 true EP0004408B1 (de) 1981-11-11

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JP (1) JPS54130504A (de)
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Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2962197D1 (en) * 1978-07-24 1982-03-25 Shell Int Research A process for preparing 1,7-octadiene
US4229605A (en) * 1978-12-13 1980-10-21 Shell Oil Company 1,7-Octadiene process
US4229606A (en) * 1978-12-13 1980-10-21 Shell Oil Company 1,7-Octadiene process
JPS57204507A (en) * 1981-06-12 1982-12-15 Nec Corp Interference film type optical multiplexer and demultiplexer
US4554375A (en) * 1984-03-15 1985-11-19 Texaco Inc. Co-preparartion of 2,7-octadienyl formate, 1,6-octadiene and 4 vinylcyclohexane from butadiene using a platinum catalyst
US4943670A (en) * 1989-11-22 1990-07-24 Shell Oil Company Preparation of conjugated dienes
JPH086253Y2 (ja) * 1991-07-15 1996-02-21 株式会社櫛田度器製作所 標 尺
US7988848B2 (en) 2005-04-15 2011-08-02 Exxonmobil Research And Engineering Company Activating hydroprocessing catalysts using carbon monoxide and use of catalysts for hydroprocessing
US20060234860A1 (en) * 2005-04-15 2006-10-19 Brignac Garland B Activating hydroprocessing catalysts using carbon monoxide
DE102007023515A1 (de) 2006-07-05 2008-01-10 Evonik Degussa Gmbh Verfahren zur Herstellung von Dienen durch Hydrodimerisierung

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3732328A (en) * 1969-10-17 1973-05-08 Ici Ltd Process for the production of octadienes
GB1344887A (en) * 1971-08-18 1974-01-23 Imp Chemical Ind Ld Production of olefines
GB1341324A (en) * 1972-06-28 1973-12-19 Ici Ltd Production of olefines

Also Published As

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EP0004408A2 (de) 1979-10-03
JPS6230169B2 (de) 1987-07-01
DE2961297D1 (en) 1982-01-14
EP0004408A3 (en) 1979-10-31
JPS54130504A (en) 1979-10-09

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